Carbon tetrabromide → Tert-butyl (4-bromobutyloxy)acetate

HRID 1271250Notes

Reaction equation

HRID 1271250 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12]O)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>ClCCl>[C:1]([O:5][C:6](=[O:14])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:35])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 865924582-(4-hydroxybutyloxy)acetic Acid Tert-Butyl Ester

Product 1

HCID 86592459Tert-butyl (4-bromobutyloxy)acetateYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17.02 g of 2-(4-hydroxybutyloxy)acetic acid tert-butyl ester in 400 ml of dichloromethane, 24.04 g of triphenylphosphine and 31.78 g of carbon tetrabromide were added. After stirring at room temperature for one hour, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 16.95 g of the desired compound as a colorless oily substance.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1fcaba6f7ebf44e7827033ce248f8923
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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